• Title/Summary/Keyword: NMR study

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The Study of Donor-Acceptor Chromophores and Diketopyrrolopyrrole(DPP) Analogues (Donor-Acceptor 발색단과 디케토피롤로피롤(DPP) 유도체에 관한 연구)

  • Kim, HunSoo;Kim, SeungHoi;Park, SooYoul
    • Tribology and Lubricants
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    • v.32 no.5
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    • pp.141-146
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    • 2016
  • The diketopyrrolopyrrole (DPP) pigment is a bicyclic 8-π-electron system containing two lactam units. Typical DPP derivative pigments have melting points of over 350°C and very low solubility in most solvents, and show absorption in the visible region with a molar extinction coefficient of 33,000 dm2mol−1 and strong photoluminescence with maxima in the range 500–600 nm. X-ray structure analyses of DPP show that the whole molecule is almost in one plane. The phenyl rings are twisted out of the heterocyclic plane and the intermolecular hydrogen bonding between neighboring lactam NH and carbonyl units influences the structure of the DPP pigment in the solid state. In this study, mono-N-alkylation and mono-N-arylation were undertaken for Pigment Red 264 or Pigment Orange 73 with alkyl halide and aryl halide, respectively, in the presence of sodium tert-butoxide as a base catalyst to improve the solubility of DPP pigments and their application as CO2 indicators. The synthetic yield was in the range 11–88%. The indicator dyes are highly soluble in organic solvents and shows pH-dependent absorption (λmax 501 and 572 nm for the protonated and deprotonated forms, respectively) and emission (λmax 524 and 605 nm for the protonated and deprotonated forms, respectively) spectra. The mono-N-alkylated and mono-N-arylated DPP pigment was identified by 1H-NMR (1H-Nuclear Magnetic Resonance Spectrometer), FT-IR (Fourier Transform Infrared Spectroscopy), and MS (Mass Spectrometry). According to the results of color and hue properties obtained by a color matching analyzer, the synthesized DPP pigment material can be used as a CO2 indicator.

The Effect of Paljinhangahm-dan on Human Promyelocytic Leukemia Cells(HL-60) Death (인진항암단의 인간 전골수성 백혈병 세포 사멸 효과)

  • Lee Gun Up;Moon Seok Jae;Moon Goo;Won Jin Hee;Kim Dong Woung;Kim Hyung Kuen;Moon Young Ho;Lee Jong Bum;Yoon Jun Chul;Kim Hong Joon
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.16 no.3
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    • pp.514-520
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    • 2002
  • Paljinhangahm-dan is an Oriental herbal formulation for its ability to modulate cancer cell growth and survival. This research was performed to study the anti-cancer effects of Paljinhangahm-dan water extract(PHWE) in human pro myelocytic leukemia(HL-60) cells. After HL-60 cells were routinely cultured, tetrazolium-based colorimetric(MTT) assay was performed for cytotoxicity test. To explore the mechanism of cytotoxicity. I used several measures of apoptosis to determine whether this processes was involved in PHWE-induced cell death in HL-60 cells. In addition, the experiment was practised 1 H-NMR spectroscopy to examine molecular structure of PHWE. This study suggested that PHWE control cancer cell growth through of apoptosis with less cytotoxicity in normal cells.

Optimization of the Spreadable Modified Butter Manufacturing by Response Surface Methodology

  • Suh, Mun Hui;Lee, Keon Bong;Baick, Seung Chun
    • Food Science of Animal Resources
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    • v.32 no.6
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    • pp.783-788
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    • 2012
  • The aim of this study was to optimize the manufacturing condition of spreadable modified butter by RSM. Based on the central composite design, the degree of optimization was expressed as a SFC as a dependent variable (Y, %) determined by NMR with 23 experimental groups. Three independent variables were the contents of butter ($X_1$, 35-75%), the contents of grape seed oil ($X_2$, 15-35%), and the contents of hydrogenated soybean oil ($X_3$, 0-4%). As the result, SFC at $10^{\circ}C$ was ranged from 32.37 to 42.76%. In addition, the regression coefficients were calculated for SFC at $10^{\circ}C$ by RSREG. The regression model equation for the SFC was $Y=39.18-0.04X_1X_3$. Consequently, the optimal contents for manufacturing spreadable modified butter were determined as 55.18% for butter, 40.78% for grape seed oil, and 4.08% for hydrogenated soybean oil, respectively. The predicted response value for SFC at $10^{\circ}C$ was 30.20%, comparable to the actual experimental SFC value as 29.85%. Finally hardness and spreadability in reference butter and spreadable modified butter produced under the optimal conditions was measured. The hardness in spreadable modified butter was 31.80 N as compared to 69.92 N in reference butter. The spreadability in spreadable modified butter was 5.6 point as compared to reference butter. This difference may be due to the contents of solid fat by butter and hydrogenated soybean oil. This study showed that the SFC value at $10^{\circ}C$ could be a suitable indicator for the manufacturing spreadable modified butter to predict important attributes such as mouth feel, hardness and spreadability.

Inhibitory Activity of Aralia elata Leaves on Protein Tyrosine Phosphatase 1B and α-Glucosidase (참두릅 잎의 Protein Tyrosine Phosphatase 1B와 α-Glucosidase 저해 활성)

  • Cho, Yoon Sook;Seong, Su Hui;Bhakta, Himanshu Kumar;Jung, Hee Jin;Moon, Kyung Ho;Choi, Jae Sue
    • Korean Journal of Pharmacognosy
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    • v.47 no.1
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    • pp.29-37
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    • 2016
  • Anti-diabetic potential of the leaves of A. elata through the inhibitory activity on PTP1B and ${\alpha}$-glucosidase has not been reported. In this study, the EtOAc fraction of methanolic extract from the leaves of A. elata showed potent inhibitory activity against the PTP1B and ${\alpha}$-glucosidase with $IC_{50}$ value of $96.29{\pm}0.3$ and $264.71{\pm}14.87{\mu}g/mL$, respectively. Three known triterpenoids, oleanolic acid, oleanolic acid-28-O-${\beta}$-D-glucopyranoside and oleanolic acid-3-O-${\beta}$-D-glucopyranoside were isolated from the most active EtOAc fraction. We determined the chemical structure of these triterpenoids through comparisons of published nuclear magnetic resonance (NMR) spectroscopic data. Furthermore, we screened these triterpenoids for their ability to inhibit PTP1B and ${\alpha}$-glucosidase over a range of concentrations ($12.5-50{\mu}M$). All three terpenoids significantly inhibited PTP1B in a concentration dependent manner and oleanolic acid effectively inhibited ${\alpha}$-glucosidase. In addition, these compounds revealed potent inhibitory activity with negative binding energies toward PTP1B, showing high affinity and tight binding capacity in the molecular docking studies. Therefore, the results of the present study clearly demonstrate that A. elata leaves and its triterpenoid constituents might be beneficial in the prevention or treatment of diabetic disease.

Development of Antitoxic Agents from Sophora flavescens Ait. (고삼 추출물을 이용한 해독물질의 개발)

  • 양희태;정승일;이영철;윤경아;백승화
    • The Korean Journal of Food And Nutrition
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    • v.15 no.1
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    • pp.36-41
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    • 2002
  • The aim of this study was to assess the antitoxic compounds, flavanones(Leachianone A=LA and Sophoraflavanone G=SFG), from Sophora flavescens(S. flavescens). We investigated the possibility of antitoxicity of LA and SFG against NIH 3T3 fibroblasts cell lines using calorimetric MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl -2H-tetra-azolium bromide] assay. The results were as follows : After cadmium was treated against NIH 3T3 cell lines, we determined IC$\_$50/. Accordingly we have examined the detoxification effects of S. flavescens, LA and SFG under cadmium IC$\_$50/=12.5$\mu$M and was carried out to observe morphological changes by the light microscopic study In NIH 3T3 cells, Sophora flavescens, LA, SFG and LA + SFG showed inhibitory effects on the cytotoxicity of cadmium and these detoxication effects increased in proportion to the concentration of these drugs. These results suggest that LA and SFG from S. flavescens retain a potential antitoxic activity.

Functionalized Emulsion Styrene-Butadiene Rubber Containing Diethylaminoethyl Methacrylate for Silica Filled Compounds

  • Park, Jinwoo;Kim, Kihyun;Lim, Seok-Hwan;Hong, Youngkun;Paik, Hyun-jong;Kim, Wonho
    • Elastomers and Composites
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    • v.50 no.2
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    • pp.110-118
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    • 2015
  • In this study, diethylaminoethyl methacrylate-styrene-butadiene terpolymer (DEAEMA-SBR), in which diethylaminoethyl methacrylate (DEAEMA) was introduced to the SBR molecule as a third monomer, was synthesized by cold emulsion polymerization. It is expected that amine group introduced to a rubber molecule would improve dispersion of silica by the formation of hydrogen bond (or ionic coupling) between the amine group and silanol groups of silica surface. The chemical structure of DEAEMA-SBR was analyzed using proton nuclear magnetic resonance spectroscopy (H-NMR), Fourier transform infrared spectroscopy (FTIR), gel permeation chromatography (GPC) and differential scanning calorimetry (DSC). Then, various properties of DEAEMA-SBR/silica composite such as crosslink density, bound rubber content, abrasion resistance, and mechanical properties were evaluated. As a result, bound rubber content and crosslink density of DEAEMA-SBR/silica compound were higher than those of the SBR 1721 composite. Abrasion resistance and moduli at 300% elongation of the DEAEMA-SBR/silica composite were better than those of SBR 1721 composite due to the high bound rubber content and crosslink density. These results are attributed to high affinity between DEAEMA-SBR and silica. The proposed study suggests that DEAEMA-SBR can help to improve mechanical properties and abrasion resistance of the tire tread part.

Ab initio and DFT Study for the Internal Rotations of Cyclopropyldifluoroborane Molecule (Cyclopropyldifluoroborane 분자의 내부회전에 대한 이론적인 연구)

  • Kim, Gyeong-Lee;Lee, Jeong-Gyeong
    • Journal of the Korean Chemical Society
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    • v.50 no.4
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    • pp.291-297
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    • 2006
  • The equilibrium structures, relative energies and NBO analyses for the possible conformations and transition states which can exist on the internal rotation of CPDFB and CPCFB molecules have been investigated using DFT and ab initio methods with various basis sets. The interaction between bonding orbital ((C1-C3, C2-C3)) and antibonding orbital (n*(B9) and *(B9-Cl11)) was the main characteristic hyperconjugation in both molecules. In addition, the stabilization energy of CPDFB was 6.63kcal/mol and that of CPCFB was 6.97(E-form)/6.79(Z-form) kcal/mol for each conformation. The rotational barriers by internal rotation of BF2- and BFCl- functional groups were evaluated to be 5.3~6.7kcal/mol and 5.7~6.5kcal/mol respectively, which showed good agreement with the experimental values reported by previous dynamic NMR study. Finally, Z-form was more stable than E-form by 0.2 kcal/mol in CPCFB molecule and therefore Z-form was confirmed as global minimum.

Characteristics of Bio-oil by Pyrolysis with Pig Feces (돈분을 이용한 열분해공정 바이오오일의 특성)

  • Kun, Zhu;Choi, Hong L.
    • Journal of the Korea Organic Resources Recycling Association
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    • v.16 no.4
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    • pp.57-63
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    • 2008
  • The characteristics of the bio-oil produced by the pyrolysis process with pig feces was investigated in this paper. The continuous auger-type reactor produced bio-oil was maintained at the temperature range of 400 to $600^{\circ}C$, which was higher than a typical that in a conventional pyrolysis system. The pig feces was used as the feedstock. The bio-oil and its compositions were characterized by water analysis, heating values, elemental analysis, bio-oil compounds, by Gas Chromatography/Mass Spectrometry (GC/MS), and functional group by $^1H$ NMR spectroscopy. It was found that the maximum bio-oil yields of 21% w.t. was achieved at $550^{\circ}C$. This result suggested that this auger reactor might be a potential technology for livestock waste treatment to produce bio-oil because it is able to be improved to reach higher efficiency of bio-oil production in further study. The pyrolysis system reported herein had low heat transfer into the feedstock in the auger reactor so that it needs improve the heat conduction rate of the system in further study.

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Synthesis and Characterization of Ir(H)(CO)(PEt3})22-C60)

  • Lee, Chang-Yeon;Lee, Gae-Hang;Kang, Hong-Kyu;Park, Bo-Keun;Park, Joon-T.
    • Bulletin of the Korean Chemical Society
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    • v.28 no.11
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    • pp.1958-1962
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    • 2007
  • The title complex, Ir(H)(CO)(PEt3)2(η 2-C60) (2), has been prepared by the reaction of excess C60 (4 equiv) with a tetrairidium complex Ir4(CO)8(PEt3)4 (1) in refluxing chlorobenzene in 40% yield as green crystals. Compound 2 has been characterized by cyclic voltammetry (CV), spectroscopic methods (mass, IR, 1H and 31P NMR), and a single crystal X-ray diffraction study. The molecular structure reveals that the iridium atom of 2 is coordinated by two axial ligands of a hydrogen atom and a carbonyl group, and three equatorial ligands of two phosphorus atoms and an η 2-C60 moiety. The CV study exhibits three reversible one-electron redox waves for the successive reductions of 2, together with additional four redox waves due to free C60 reductions, which was formed by decomposition of 2 in the reduced states. The three reversible redox waves of 2 are shifted to more negative potentials by ca. 270 mV compared to free C60, reflecting both metal-to-C60 π-back-donation and the electron-donating nature of the two phosphorus ligands.

Isolation of Anticancer Compounds from Peucedanum japonicum Thunb. Roots

  • Jun, Neung Jae;Kim, Seong-Cheol;Song, Eun-Young;Jang, Ki Chang;Lee, Dong Sun;Cho, Somi K.
    • Korean Journal of Plant Resources
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    • v.27 no.3
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    • pp.215-222
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    • 2014
  • This study was conducted to isolate a compound with anticancer properties from the roots of Peucedanum japonicum Thunb. (Umbelliferae), and to evaluate the efficacy of that compound's anticancer activity. The $CHCl_3$ layer was purified via repeated column chromatography and recrystallization. The two compounds isolated from $CHCl_3$ layer were identified via NMR spectroscopic analysis as (10E) 1,10-heptadecadiene-4,6-diyne-3,8,9-triol (Comp. I) and anomalin (Comp. II). (10E) 1,10-heptadecadiene-4,6-diyne-3,8,9-triol was the first report from the roots of P. japonicum. MTT assays were conducted to evaluate the in vitro cytotoxic activities of Compounds I and II against the following human cancer cell lines: HeLa, HepG2, SNU-16, and AGS. Comp. I evidenced the most profound cytotoxic activity against HepG2 cells ($IC_{50}=6.04{\mu}g/mL$), and Comp. II exhibited the most profound cytotoxic activity against SNU-16 cells ($IC_{50}=18.24{\mu}g/mL$) among the human cancer cell lines tested in this study. However, no significant cell death was observed in the CCD-25Lu human normal lung fibroblast cells. Quantitative analysis using UPLC (Ultra Performance Liquid Chromatography) showed that the roots of P. japonicum contained 0.015 (Comp. I) and 1.69 mg/g (Comp. II) of these compounds.